4-Bromophenacyl bromide → 2-Amino-5-(4-bromophenyl)pyrrole-3-carboxamide

HRID 1011565Notes

Reaction equation

HRID 1011565 reaction equation
[O-]CC.[Na+].[CH2:5]([C:9]([NH2:11])=[O:10])[C:6]([NH2:8])=[NH:7].Cl.Br[CH2:14][C:15]([C:17]1[CH:22]=[CH:21][C:20]([Br:23])=[CH:19][CH:18]=1)=O>C(O)C>[NH2:7][C:6]1[NH:8][C:15]([C:17]2[CH:22]=[CH:21][C:20]([Br:23])=[CH:19][CH:18]=2)=[CH:14][C:5]=1[C:9]([NH2:11])=[O:10]

Participants

5

Reactant 3

HCID 74544-Bromophenacyl bromideHCID 2723922Sodium ethoxideHCID 3084595Amidinomalonamide hydrochloride

Product 1

HCID 592859782-Amino-5-(4-bromophenyl)pyrrole-3-carboxamideYield 9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Under ice-cooling, sodium ethoxide (2.1 g, 30 mmol) was added to a suspension of malonamamidine hydrochloride (4.1 g, 30 mmol) in dehydrated ethanol (50 mL), and then the mixture was stirred for 20 minutes. Moreover, 2,4′-dibromoacetophenone (4.2 g, 15 mmol) was added thereto, and the whole was stirred at room temperature for 5 hours. After the insoluble solid was filtered out, the filtrate was concentrated in vacuo. The obtained residue was purified by silica gel column chromatography to give the title reference compound (0.37 g) as a black solid (Yield 9%).

Workup

  1. temperatureUnder ice-cooling
  2. stirringthe whole was stirred at room temperature for 5 hours
  3. filtrationAfter the insoluble solid was filtered out
  4. concentrationthe filtrate was concentrated in vacuo
  5. customThe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-b2436f09308e4ebf8d1fc7d84b09038e
Source dataset
uspto-grants-2011_07
Patent number
US07977371B2

Reaction notes

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